Kiyosaki's earlier two businesses (for surfing bags with Velcro fasteners and T-shirts) went bankrupt.Thereafter he set up a company for financial and real estate education that has done well thus far, with its main business model of high priced seminars (ranging from $12,000 to $50,000 per head).[] In an interview with CBC, he described his books as an advertisement for his higher priced seminars. In 2012, Kiyosaki again filed for bankruptcy.

Kiyosaki operates other external business ventures and investments. Many are concentrated in the information technology (mobile apps and internet), publishing, retail, education, mining, energy, financial market, and real estate industries. Kiyosaki asserts that he makes 2 million USD in cash flow per month tax free from all his businesses and investments. Kiyosaki's estimated wealth is about $80 million USD. Kiyosaki is involved with the apartment business and owns over 1400 units of apartment houses. Kiyosaki has been involved with commercial real estate sector such as investing in warehouses, Triple net lease and real estate development ventures around the United States.

During the subprime mortgage crisis in the late 2000s, Kiyosaki invested heavily having acquired nearly 40% of his 2015 portfolio of distressed properties during the downturn. In 2008, Kiyosaki purchased a 300 unit, $17 million apartment complex in Tulsa, Oklahoma. Many of his commercial real estate holdings include luxury and boutique hotels, golf courses, and large apartment complexes according to an interview he did with The Alex Jones Show in 2010. During the same year, Kiyosaki acquired a $46 million Arizona landmark resort with 5 golf courses that was in foreclosure at a bankruptcy court. In 2011, he invested in a 2000 unit apartment construction project and earned approximately $250,000 in monthly cash flow. In May 2015, he invested in a 1600 unit apartment complex for $80 million USD. In December 2015, Kiyosaki refinanced a $300 million mortgage at 2.5 percent on one of his apartment complex investments. In May 2016, Kiyosaki stated he controls over 10,000 apartment units producing over one million dollars in cash flow every month. Kiyosaki has been in the oil business since the late 1990s. He owns a number of oil drilling operations and oil wells in Texas, Louisiana, and Oklahoma. In 2013, Kiyosaki invested in three new oil wells at a 10 percent stake. In late 2015, Kiyosaki amassed a portfolio of 400 privately controlled oil wells